I can second Eddie. I would also add that if he doesn’t currently have what you are looking for, he can probably find it relatively quickly. He found a 16220 DJ for me that would fit your price limits. I don’t know if a DJ fits your criteria, but if you tell him your parameters, I’m fairly certain he will be able to help you get the most watch for the least money.
Breitling is well known. The old emergency is cool. But I’m a Blancpain fan and there are some available near 5k. Or Breguet
Another shout out to @flat_plane_eddie - Who is THE ONLY source I would deal with for any watch other than my ADs -
To add to this - I recently bought a vintage Datejust. I own a Submariner too, but this Datejust really is super versatile. It goes with anything I want to wear, can be dressed up or dressed down with the change of a strap. I love the Sub, but it just doesn't seem to have this versatility. And it won't take a depreciation hit either. PDG
I vote for a Rolex Explorer I. Great watch that you can wear anywhere. Depending on what model you get, I have seen them starting at a little over $5k or you could get on a waiting list and probably get a new one for MSRP, which is about $7200 or if you want the discontinued 39mm they are probably $8-10k. A submariner is another great choice.
I have a couple of Speedmasters, and recommend them. But I also like the IWC offerings. Both brands are, I believe, in your price range.
Thanks for the feedback and have been doing some virtual shopping (although not planning to buy until later in the year). I have a thing for the VC Overseas, and there appears to be some SS models for $10k-ish. Probably from the previous century though.
Less traditional option: Casio G-Shock GMW-B5000TVA. Titanium, solar, atomic radio time sync, bluetooth etc... Or for 10x the price, Tag Heuer F1 x Mario Cart... Image Unavailable, Please Login
As a CPA, I learned to never wear a watch nicer than my clients. My current watch costs $100. The band cost $400. Works for me. I gave my Rolex to my SIL. I love to watch salesmen check me out with no jewelry, cheap watch, scruffy shoes, and cheap haircut. Sent from my iPhone using FerrariChat.com mobile app
1980s_1990s Speedmaster. Best bang for the $5-8k budget. These are the last of the tritium markers and hands with have great movements. Vintage look, very easy to wear on bracelet or strap. Neo-classic. Just an example: I’m not proposing this specific piece…or this specific seller (however he is well regarded and specializes in Speedies). https://www.chronoholic.com/product-page/1995-omega-speedmaster-professional-3590-50-full-set-1